It seems that Hefner, who just turned 83, is something of a hopeless romantic, according biographer Steven Watts, author of Mr. Playboy: Hugh Hefner and the American Dream, who says his subject is "in love in with love." So what does Hef make of his own as they move on from life behind the Mansion walls?
Holly Madison, split from illusionist Criss Angel
"My conviction has always been, being an romantic, that the best solution for a failed romance is a new romance," Hefner says.
Bridget Marquardt, whose new boyfriend is director Nick Carpenter
"The major problem for her, quite frankly, is that she's not here a lot. She's got this wonderful dream job for the Travel Channel, she's wandering the globe. We'll see how that plays out, whether she's really contemplating making this more serious."
Kendra Wilkinson, who is marrying NFL star Hank Baskett in June
"I've been very lucky in romance, but not expert in marriage (two divorces). "They are two separate things. What happens traditionally in a marriage is, of course, a marriage turns into parenthood and the affection is kind of transferred to the children. She picked very well, I think he adores her, I think she really loves him. What they have to get over is they come from very different backgrounds. If love conquers all, it'll conquer them."
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